The Turning-65 Checklist: 8 steps before your 65th birthday

The 8-step checklist

1. 1

   Mark your 7-month Initial Enrollment Period on the calendar

   Your Initial Enrollment Period covers seven months: the three months before the month you turn 65, your birthday month, and the three months after. If your birthday falls on the first of the month, everything shifts one month earlier. Write the actual dates down. Knowing this window cold is what keeps the rest of the process on track.

2. 2

   Decide: are you still working with employer coverage?

   If you are 65, still working, and covered by an employer group plan with 20 or more employees, you can usually delay Part B without a late penalty. When the job or the coverage ends, you get an 8-month Special Enrollment Period. But COBRA and retiree coverage do not count as active employment coverage. If the company has fewer than 20 employees, you generally need to enroll at 65. Get this decision right before you do anything else, because it drives every step below.

3. 3

   Sign up for Part A

   Part A (hospital insurance) is premium-free for most people who paid Medicare taxes for at least 10 years. There is rarely a reason to delay it. You can enroll online at ssa.gov, by phone, or in person at a Social Security office. If you are already receiving Social Security benefits, you will be enrolled automatically.

4. 4

   Make the Part B decision carefully

   Part B (medical insurance) has a monthly premium, and the late enrollment penalty is 10% of the premium for every 12-month period you were eligible but did not enroll, and it lasts as long as you have Part B. This is the penalty that actually sticks. If you are delaying because of employer coverage, confirm the coverage qualifies (see step 2). If you are not sure, ask before your window closes, not after.

5. 5

   Choose your path: Original Medicare plus supplements, or Medicare Advantage

   You have two main ways to get your coverage. Original Medicare (Parts A and B) plus a Medigap supplement plus a Part D drug plan, or a Medicare Advantage plan (Part C) that bundles things together. Neither is right for everyone. Medigap gives you predictable costs and any-doctor flexibility. Advantage often has lower premiums and extra benefits but works through networks. This is the decision worth sitting down over, not making from a TV commercial.

6. 6

   Do not miss the Medigap open enrollment window

   This is the one people miss most often. When you are 65 or older and enrolled in Part B, you get a one-time 6-month Medigap open enrollment period. During it, insurers cannot deny you or charge more because of health problems. Outside this window, they can ask health questions and turn you down in most states. If you think you might ever want Medigap, this window is the time.

7. 7

   Line up your prescriptions

   Whether you go the Part D route or an Advantage plan with drug coverage, pull your current medication list and check each drug against the plan's formulary. Drug lists change every year, and a medication that is affordable on one plan can be expensive or uncovered on another. Bring the actual list, with dosages, to any enrollment conversation.

8. 8

   Confirm your doctors are covered

   Before you enroll in anything with a network, verify your primary care doctor, your specialists, and your preferred hospital are in that specific plan's network. 'Takes Medicare' and 'in my plan's network' are two different things. Call the doctor's office and ask about the plan by name, or check the plan's provider directory and then confirm by phone.

Step 5 is the big fork in the road. If you want the full comparison, here is Advantage versus Medigap in plain English. And for the real dollar picture, here is what Medicare costs.